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If the parent is the recipient, box 6 should be checked. If the student is the recipient, box 6 should not be checked. The wording is awkward and you are smart to look at what the program is doing. You want your forms going to the IRS to be correct regardless of the program. Answer whichever way makes the form correct.   I recommend you let the developers know. Once you file your return, as long as the settings to receive communication from Intuit don’t block it, you will see a pop-up message or receive an email with a survey asking you about your experience. We encourage you to leave your notes and comments there. “Voice of the Customer” notes and comments are read and acted upon.  If you are using TurboTax Desktop, you can also leave feedback at the Final Steps tab.

If you are being required to choose between the General Rule and Simplified Method, rather than using the amount from your Form CSA 1099-R, it is likely due to the "Taxable Amount" follow-up question.    When you reach, "For the years you received these distributions, was the total amount shown in the form the amount you paid tax on?":   If you answer "No", TurboTax will assume that you have "basis" consisting of after-tax contributions that have not been fully recovered yet. It will then force the Worksheet to ensure you are not paying tax on your own money twice.   If the amount in Box 2a is already correct and you want to bypass the Worksheet, answer "Yes". TurboTax will assume the entire distribution is taxable (or that the taxable amount was already handled, as in your case) and should stop asking for those details.   If you do need to use the worksheet, you will need the following information:   Annuity start date Plan Cost (Basis), which is the amount of after-tax money you (or your employer) contributed to the plan (Usually shown in Box 9b of your 1099-R) Age at start Amounts previously recovered, which is the total amount of "tax-free" principal you've already claimed on prior years' returns